Hydrochloric Acid → HCID 86623161, compound

HRID 1170935Notes

Reaction equation

HRID 1170935 reaction equation
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].[Li]CCCC.C[O:14][C:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([CH3:23])[CH:17]=1.Cl>C1COCC1.CCCCCC.O1CCOCC1>[CH3:4][O:3][P:2]([CH2:1][C:15]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([CH3:23])[CH:17]=1)=[O:14])(=[O:7])[O:5][CH3:6]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 12958Dimethyl methylphosphonateHCID 18788764Methyl 4-fluoro-3-methylbenzoateHCID 178418339Butyllithium

Product 1

HCID 86623161HCID 86623161, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 19.2 g (155 mmol) dimethyl methylphosphonate in 150 mL THF at −70° C. was added 97 mL (155 mmol) 1.6M n-BuLi in hexane. The mixture was stirred for 45 min and a solution of 11.8 g (70 mmol) 4-fluoro-3-methyl-benzoic acid methyl ester in 15 mL THF was added. After 15 min at −70° C. the mixture was allowed to warm to 0° C. and neutralized with 4N HCl in dioxane. The mixture was diluted with 500 mL THF to obtain [2-(4-fluoro-3-methyl-phenyl)-2-oxo-ethyl]-phosphonic acid dimethyl ester. 6 mmol [2-(4-fluoro-3-methyl-phenyl)-2-oxo-ethyl]-phosphonic acid dimethyl ester in THF was stirred together with 0.5 g (4.6 mmol) pyrimidine-5-carboxaldehyde and 1.65 g Cs2CO3 for 16 h at room temperature. The mixture was diluted with NH4Cl aq. and ethyl acetate. The organic layer was separated, dried with MgSO4 and evaporated to dryness. The residue was used crude in the consecutive step.

Workup

  1. waitAfter 15 min at −70° C. the mixture was allowed

Sources & evidence

ORD record
ord-30c5e2e8a9f04f3fad02c051b1ca0644
Source dataset
uspto-grants-2010_11
Patent number
US07829563B2

Reaction notes

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